I'm gay and a junior in high school, and I've had a boyfriend for a year. We are out to our parents and everyone is supportive. But we are frustrated! We had sex education in our schools, but they didn't cover gay sex. (Big surprise!) I tried to talk to my mom about gay sex, and all she said was "please use condoms." We tried, but we must be doing something wrong because we can't do it. We are ready to have real gay sex — with me on the bottom, at least for now — and we feel like failures as gay men.
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P.S. Do we really need to use condoms? We are both each other's first boyfriend.
You and your boyfriend aren't failing gayness, TUSH.
Gay men and boys can be successes in life, in love and in the sack without acing — or even enjoying — anal intercourse. There are many ways that you can get off that are just as pleasurable, just as "real" and just as gay as anal intercourse. But if you and your boyfriend want to give anal another go, here's a crash course ...
First, experiment on your own. Use fingers and toys and lots of lube. I recommend that you get your hands on a butt plug and get yourself off with that butt plug in your ass. Exploring anal penetration solo will allow you to experience anal pleasure without pressure or expectations.
Your boyfriend should do the same. I don't care if he is a top: He will be a better top if he knows what it feels like to be penetrated and enjoys penetration himself.
OK! So you've both done some exploring on your own. Your butts are squeaky clean and, hey, you've got the house all to yourselves ... is it time to fuck? Not yet. Now you're gonna spend some time sticking fingers and toys in your butts and jerking off together. You can experiment with rimming, as nothing relaxes anal sphincters quite so effectively. (Once more with feeling: squeaky-clean butts!) The point is for you to do anal and for both of you to get off — without his dick going anywhere near your ass.
Now you're ready to get fucked.
You're going to need lots of lube, and lots of patience. Have your boyfriend apply lube directly to your hole; he should gently rub your hole for a bit, to help it relax, before pushing some lube just inside; you can apply the lube to his dick. Move into whatever position feels most comfortable, and point the tip of his cock directly at your hole. He should apply some pressure: uniform, constant, gentle pressure. You'll feel your asshole open as his cock enters you. Keep breathing as the rest of his dick slowly — a fraction of an inch at a time — slides into you.
Once he's all the way inside, your boyfriend may be tempted to start banging away, but that would be a huge mistake. He should stay perfectly still for a minute or two while you breathe and relax. Kiss your boyfriend and stroke yourself during the lull. Then he starts moving inside you — very slowly. He pulls out an inch or two and slides back in, you keep breathing and stroking, he pulls back an inch or two more and slides in. With each thrust, your boyfriend will be able to pull out a little farther: Before you know it, he'll be fucking the hell out of you. The whole process (the hole process?) takes 30 minutes at least.
P.S. You don't have to use condoms, but you should. Using condoms is a good habit to get into, and if you have concerns about cleanliness, a condom is your best friend. There are lots of gay guys — including guys as young as you — who got infected with HIV by boyfriends who lied or didn't know or fucked up. So listen to your mother and use condoms, along with a water-based lubricant.
I am an intern at the health and wellness center at my university. This is safe-sex-awareness month on campus. We got donations from some sex-toy companies. Among the products we received is something marketed as "Desensitizing Anal Wipes."
We gave away these samples at our recent expo. After the fair, a student expressed concern that desensitizing anal wipes were not safe to use, as masking pain could lead to engaging in activities that you may not otherwise. I am assuming that what he meant here is that if you are experiencing pain during anal sex, you probably shouldn't proceed. I'd like to know what the Dan Savage take is on anal desensitizing wipes.
A Sensitive Subject
Googling "desensitizing anal wipes" got me this: "perfect for using before anal sex to reduce friction pains and ease entry."
Anyone who's too stupid to use lube for anal sex — or anyone who is using lube but somehow doesn't realize that reducing friction and easing entry is what lube is for — probably won't be harmed by a "desensitizing" moist towelette. I don't know what the active ingredient is, ASS, but I can't imagine it's a pharmaceutical-grade topical anesthetic. So I doubt that anyone using a DAW will wind up with an ass so benumbed that he won't realize he's being torn to shreds until after he sees blood and santorum all over his sheets, pillows, walls, floor, boyfriend, Xbox 360, cats, etc.
That said, desensitizing anal wipes play on common misconceptions about anal sex — namely, that anal sex is supposed to hurt. Anal done right isn't painful, even if it takes time, practice and some patience to get used to. Some people do experience discomfort when they first attempt anal, but discomfort isn't pain. It's important for people to understand that if anal sex hurts, they're doing it wrong and they need to stop. Desensitizing wipes send the opposite message.
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